This walking tours itinerary reshuffles the schedule around walking tours activities — neighborhood walks and self-guided exploration. A moderate mix of walking and active experiences, with plenty of guided experiences. Includes 4 must-see landmarks across Miami and Upper Keys and Marathon.
Highlights: South Beach & Art Deco District, Wynwood Walls & Design District, Little Havana, Turtle Hospital
This 14-day Florida Keys walking itinerary covers Miami, Upper Keys, and Marathon on foot — 18 walking-focused activities take you through neighborhoods, markets, and landmarks at street level.
Your Route — ordered to minimize backtracking
25+ activities scored and ranked · route optimized across 3 cities
Day-by-Day Schedule — heavy and light days alternate so you don’t burn out
Miami
MiamiStroll the iconic Art Deco Historic District and soak up South Beach's vibrant oceanfront scene
Best Nov-Apr (dry season). Jun-Nov is hurricane season with afternoon thunderstorms.Discover world-class street art murals and cutting-edge galleries in Miami's creative heart
$13 Verified Mar 2026 Open daily 10:30am-6:30pm year-round. Best Nov-Apr to avoid summer heat.South Beach / Mid-Beach / Brickell
Experience Miami's Cuban soul with cafecito, cigars, live salsa, and Domino Park on Calle Ocho
Year-round destination. Best Nov-Apr for comfortable walking weather.Explore Wynwood with a small group and learn directly from a local expert. On this graffiti tour, explore this artistic
$39 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Enjoy a personalized adventure led by your very own private guide. Join a Miami local to experience the sites of Wynwood
$53.34 Verified Mar 2026 Book this tour →Explore Wynwood with a small group and learn directly from a local expert. On this art and beer adventure, you’ll love g
$67.16 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Explore Wynwood with a small group and learn directly from a local expert. As part of this Cycle Party, you'll pedal you
$44.8 Verified Mar 2026 Book this tour →Enjoy a personalized adventure led by your very own private guide. This historical tour of Miami immerses you in the cit
$197.75 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Enjoy a personalized adventure led by your very own private guide. This half day tour is a great way to begin your trip
$197.75 Verified Mar 2026 Book this tour →With the step-by-step guidance in your personalized App Guide, create your own adventure and explore at your own pace. D
South Beach / Mid-Beach / Brickell
With the step-by-step guidance in your personalized App Guide, create your own adventure and explore at your own pace. E
Get ready to party. On this tour, you and your friends will take a party bike on a two-hour bar crawl to three bars in t
$42 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Enjoy a personalized adventure led by your very own private guide. Get comfortable as you join your driver in a luxury c
$248.61 Verified Mar 2026 Book this tour →Avoid the hassle of transport, traveling to with a small group and the support of a local guide. This is recommended fo
$219 Verified Mar 2026 Book this tour →South Beach / Mid-Beach / Brickell
Escape to Key Biscayne for pristine beaches, the historic Cape Florida Lighthouse, and kayaking
$8 Verified Mar 2026 Open 8am-sundown daily. Arrives early on weekends — park closes at capacity.Drive the Overseas Highway to Key Largo and Islamorada for snorkeling, wildlife, and island vibes
Best Nov-Apr. Hurricane season Jun-Nov.South Beach / Mid-Beach / Brickell
Sail Biscayne Bay on a private charter with skyline views, snorkeling, and sunset options
Year-round. Calmest waters Nov-May.Explore Miami Zoo, the Children's Museum, and Jungle Island with the whole family
Year-round. Indoor/outdoor mix works in any weather.South Beach / Mid-Beach / Brickell
Upper Keys
Upper KeysDrive the full Overseas Highway to Key West for Old Town, Duval Street, and a sunset celebration
Year-round. Best Nov-Apr for comfortable weather.Head north to Miami for South Beach, Wynwood Walls, and Little Havana's Cuban cuisine
Year-round. Best Nov-Apr.Key Largo / Upper Matecumbe Key / Venetian Shores
Explore the Everglades with a small group and learn directly from a local expert. On this small group "Day in the Glades
$160 Verified Mar 2026 Book this tour →Key Largo / Upper Matecumbe Key / Venetian Shores
Marathon
MarathonDrive the scenic Overseas Highway from Marathon to Key West for a full day of island exploration
Year-round. Best Nov-Apr for comfortable weather.Tour the only state-licensed sea turtle veterinary hospital and meet rescued turtles up close
$35 Verified Mar 2026 Open year-round, tours on the hour 9am-4pm. Book in advance — spots fill quickly. Book this tour →Vaca Key / Sombrero Beach / Boot Key Harbor
Meet Atlantic bottlenose dolphins at this nonprofit marine research and education facility
$35 Verified Mar 2026 Open daily 9am-4:30pm year-round. Interactive programs book separately.Snorkel or dive the vibrant patch reefs off Marathon with small-group or private boat trips
Best visibility Apr-Oct. Winter seas can cancel trips.Vaca Key / Sombrero Beach / Boot Key Harbor
Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Marathon!
Where You’ll Stay
Estimated total: $2,016–$3,024
Trip Budget Estimate
Estimates based on listed activity prices and hotel rates. Actual costs vary by season, availability, and personal spending.
Typical range for Florida Keys
$1,400 – $7,000 per person for 14 days
Similar Destinations
Similar vibes, fewer crowds — destinations our algorithm rates as close matches to Florida Keys.
🧳 Practical Info for Florida Keys
- Visa
- ESTA required for Visa Waiver Program countries. CA citizens visa-exempt. See US entry requirements.
- Tipping
- 18–20% tip expected at restaurants. Standard US tipping culture applies.
- Currency
- US Dollar ($ USD). Cards accepted everywhere.
- Power
- 120V, Type A/B plugs. EU/UK/AU travelers need an adapter.
- Connectivity
- Good coverage along the Overseas Highway. Some remote keys may have weaker signal.
- Emergency
- 911 (general emergency)
🚗 Getting Around Florida Keys
Drive the Overseas Highway (US-1) from Miami through all the Keys — one of America's most scenic drives.
Keys Shuttle runs between Miami Airport and Key West with stops along the way.
Frequently Asked Questions
What is the best time to visit?
Spring and fall offer the best weather and fewer crowds. Summer is peak season. Check regional weather patterns for specific conditions.
Do I need to rent a car?
A car is essential for road trips and national parks in the US. Public transit is limited outside major metro areas.
How much does a week cost?
Budget: $100-150/day. Mid-range: $200-350/day. Luxury: $500+/day. Costs vary significantly by region and season.
